The 1950s HousewifebyTravel_by_day©
Drew and Paul were roommates, friends from college who had only graduated less than a year ago. They both got jobs in downtown, and wanted to live close to the action. Rents were high, though, so sharing a place seemed a good idea.
Drew and Paul were sitting at home on Superbowl Sunday, watching the pre-game show. The New England Patriots hadn't lost a game all season, and were heavily favored over the New York Giants.
Drew took a swig of beer and said, "there's no hope for the Giants today."
"I don't know," said Paul. "I think they could win. It's unlikely, but it could happen."
"Not a chance," Drew said. "I'd bet my fortune on that."
"You don't have a fortune, Drew," Paul said. "You'll have to bet something that is worth more than $50 in empty beer bottles. Okay, I have a bet. If the Giants win, you have to clean the apartment and do my errands for a week."
"Hell, if the Giants win, I'll do it all wearing a French maids outfit!" Drew said.
"You're on," Paul said.
The New York Giants ended up winning the Superbowl by a score of 17 to 14 over the Patriots in what was probably the second biggest upset in Superbowl history, behind only the New York Jets beating the Baltimore Colts in Superbowl Three. Interestingly for this story, the Jets were led by "Broadway" Joe Namath, who would become famous for not only being a quarterback, but wearing pantyhose in a TV commercial.
As the post game analysis raged on the TV, Paul turned to Drew and said, "you know, I changed my mind about the French maid's outfit."
"Thank god," Drew said.
"I'd rather you dress up like a housewife from the 1950s."
"Come on, dude. You're joking, right?" Drew asked.
Paul shook his head. "Not at all. I think I'd rather have a nice bob-haired 1950s housewife fetching my slippers than some illegal French chick stealing jobs from Americans."
Drew swallowed hard. "So you want me to start dressing up like a 1950s housewife starting tomorrow?"
"No," Paul said, which gave Drew a brief moment of relief. What came next dropped the heart right out of Drew's chest, though. "Let's start it next Monday. That'll gave us time to get you the proper dresses and a nice wig. Oh, and you'll be able to use this week to get the time off work."
"Time off work? You seriously want me to take a week of vacation for this stupid bet?"
"Oh yeah, you're a 1950s housewife. You can't have a job outside the home. What kind of 1950s husband would I be if I let my wife work," Paul said, with a wink.
Drew sat silently the rest of the night, barely believing that Paul could be serious. The next morning Drew had convinced himself that Paul was joking, but as Drew was leaving, Paul said, "Don't forget to get next week of work, Drewina."
By the time Drew got to work, he was furious. There was no way he was going through with this bet. He only got 2 weeks of vacation a year, he wasn't going to waste one dressing up for his stupid roommate. Drew sat in a huff at his desk when he noticed an email come in from Paul.
"Here's a little inspiration for you," it said, with a link. He clicked on the link, and it popped up a website with a bunch of ads from magazines in the 1950s, showing women in dresses and aprons using household appliances and cleaners. At first, this made Drew even more angry, but as he browsed the page, he started to get curious. He went to Google and typed in "1950s housewife," and looked at the images Google brought back.
"Maybe it would be a laugh," Drew said to himself. "It'd be like the initiation rites at a Fraternity. Harmless fun, really." Drew convinced himself, and went in and got the time off work for next week.
Drew didn't tell Paul that he'd gotten the time off work, though. Drew was still afraid that perhaps Paul was joking, and that it would look really bad that he took time off from work. So Drew kept quiet, figuring that if Paul didn't mention it, he could at least use the time off to catch a last minute flight somewhere warm for a week.
On Thursday, however, Paul showed up at the apartment carrying a large number of bags. "Oh, have I got some goodies for you!" he said, and threw the bags on the couch. Paul reached in and pulled out a green and red plaid dress. "Ta-da! I had to guess at your size, but I think it'll fit. Go try it on, to see if we have to take it back."
Drew resisted at first, but eventually Paul heckled him enough, and Drew tried it on. Amazingly, it fit perfectly, though it was a little big around the chest. "I don't think I have the boobs to fill this out," Drew said, walking out from his room to show Paul.
"No problem," Paul said, and pulled out a bra. "It's waterfilled, so you can make yourself a nice B cup. I thought about getting a C-cup, but didn't want you too top heavy."
"Oh god, Paul. Are you serious?"
Paul just laughed, and started pulling more stuff out of the bags. There was a brown haired wig in a woman's bob, a white-frilled apron, a case of makeup, pantyhose and a few pairs of woman's panties. "The piece-de-resistance, though, are these." Paul pulled out a shoe box and produced a pair of black heels. "I didn't want anything too slutty, because you are a good Christian wife and all. I figured you could wear these to church on Sunday."
Drew shook his head. "There is no way I'm going to church in that get-up!"
Paul laughed, and handed Drew all the bags. "You can keep these in your room until Monday. But Monday morning, I want to wake up to my wife making me a nice eggs and bacon breakfast and a steaming cup of coffee."
So for the next few days Drew went to bed every night staring at his feminine garb. Half of him was scared, but the other half just couldn't wait for Monday to try it all on.
Monday morning, Drew set his alarm half an hour earlier to get ready. He tried applying make-up, but it ended up looking horrible. He put on his dress with pantyhose, but the hose were uncomfortable and you could see his leg hair through the hose. Drew looked at himself in the mirror and sighed. From Paul's room, he heard the Paul's alarm clock. "Oh well, best get at it."
While Paul showered, Drew brewed some coffee and made eggs and bacon. Drew grabbed the morning paper, and laid it out in front of Paul's plate of eggs. Paul emerged from his room dressed for work, and Drew met him in the hallway with a steaming cup of coffee.
"Here you go, Paul," Drew said.
"I think you should either call me sir, or 'my husband.' It sounds more formal that way," Paul said, taking the cup. Paul sat down at the table and started to eat. Drew sat across from him.
"Paul..." Drew said, but Paul put his finger to his lips.
"Remember, either 'my husband' or sir," Paul said.
Drew sighed loudly. "Okay, My Husband, can I have the sports section?"
Paul let the paper droop, a shocked expression on his face. "I hardly think it's fitting for a 1950s housewife to be interested in sports. In fact, I think a 1950s housewife would sit quietly and let her busy man eat in peace. I have a tough day of work ahead of me." With that Paul straighten up the paper and continued to read and eat his bacon and eggs.
Drew sat quietly until Paul finished. Paul got up from the table and went towards the door. "Now, I'll be home at 6 o'clock, and I'd like a few minutes to unwind with a drink and the TV before dinner. Have dinner on the table for 6:30. And one more thing, you need to do something about your legs. I'm all for this 'women's lib', but a girl really can't go that long without shaving her legs."
Paul left, and Drew stripped off his clothes. "This is so stupid," he thought, as he changed into sweat pants and a t-shirt. He cleaned the apartment for a few hours, and then sat down to watch TV. Around 5 o'clock he got up, showered and got dressed back up in his 1950s housewife garb. He again fumbled with his make-up. "Why can't I make this look good? Millions of women do this every day." He looked in the mirror, and realized that his beard was starting to show. Drew cleaned his face of makeup, shaved for the second time that day, and re-applied his makeup, taking even longer and trying to be gentle. It still looked bad, but was better than the first two attempts.
Drew looked at the time, it was almost six o'clock, and he hadn't started dinner. Drew raced into the kitchen and turned on the oven. All he was doing was heating an already cooked roast, but by the time the oven heated up and the roast was done, dinner would be later than 6:30.
Paul arrived home just after six o'clock. "Hi honey, I'm home."
Drew walked out of the kitchen. Paul looked disappointed. "What, you don't greet your husband with a drink after his tough day."
"I'm sorry, sir. What would you like," Drew spit the words out, venomously. Drew was getting tired again of this stupid bet, and any curiosity he had felt about dressing up had faded.
"A nice cold beer, please," Drew said, kicking off his shoes and sitting on the couch. Drew retreated to the kitchen and brought back a beer for Paul.
"Now you can go and fetch my slippers for my sore feet," Paul said, wiggling his toes. Drew went to Paul's bedroom and got his slippers. He returned to the living room and dropped them on the floor in front of Paul. "Now, now," said Paul. "A good wife would put the slippers on my feet." Drew snarled, but bent down and picked up the slippers.
As Drew went to put the slippers on Paul's feet, however, Paul moved his foot and brushed it along Drew's arm. Drew froze for a moment and let Paul run his foot up and down his arm. Drew's anger past, and he suddenly felt turned on.
"Umm, I have to check on dinner," Drew stammered, quickly putting the slippers on Paul's feet and heading into the kitchen. Drew leaned against the stove, trying to make sense of what was happening. He was dressed up as a woman, and his roommate had just made a pass at him. What confused Drew even more was that he liked it, and wanted it to happen. Drew realized that when he was angry at Paul before it wasn't for making him dress up like this, it was because Paul didn't comment on how he looked.
Before Drew could compose his thoughts entirely, though, Paul walked into the kitchen. "Oh, my wife, do you want to disappoint me?" he asked. Drew looked over and noticed Paul looking disappointed again.
"What it is, my husband," Drew asked.
"This kitchen is a mess. Did you just stay home all day watching your stories, instead of cleaning our house? I work very hard all day, and the only thing I ask is to come home to a clean house and a pretty wife, and I don't really feel that I'm getting either today." Paul ran his finger along the counter were some sauce from the roast had dripped. He picked up a wooden spoon that Drew had left on the counter. "Everything in its place, my wife. This shouldn't be out here. Now, how can we make sure you remember to put things away?"
Drew said he didn't know, but instinctively felt his ass pushing out and rising up.
"I think you do," said Paul, and with that he whacked Drew on the behind with the wooden spoon. Drew gasped. It was painful, but after the pain subsided he felt a jolt of joy. Paul wound up and hit Drew again, and then a few more times with the spoon. Each time, the sting of pain would last a brief moment, and then be replaced by a pleasant heat.
"Now, let's see what else you didn't do today." Paul led Drew through the house, pointing out all the cleaning errors Drew had made. Paul was most disappointed when he got to his room. "Did you clean in this bedroom at all?" Paul asked. Drew hadn't, not really wanting to go into his roommate's bedroom. "Tomorrow, I expect you to do a full cleaning of this room. Do you hear me?"
With that Paul retreated back to the couch to finish his beer. Drew walked by, and Paul didn't even move his gaze from the TV set. Drew was even more confused now. Did Paul really make a move on him when he brushed up and down his arm? Perhaps that was something Drew just imagined. Drew poured himself a shot of vodka to calm himself down. He thought for a moment, and came to the conclusion that it must be his imagination. Paul wouldn't hit on Drew. Paul wasn't gay, and neither was Drew. He put the thoughts out of his mind.
Drew pulled the roast from the oven, and started dishing it out along with some instant mash potatoes onto two plates. "Dinner's almost ready, my husband," Drew said.
Paul entered the kitchen and moved up behind Drew. Paul stood so close to Drew that the fabric of Drew's dress was brushing against Paul's pants. Paul reached around Drew and ran his finger on his plate to sop up some of the gravy. Paul's other hand steadied himself against the counter. Drew was enveloped by Paul, and it felt good. Drew pushed his ass out until it pressed hard against Paul's crotch. Drew couldn't tell for sure through the fabric of the dress, but it felt like Paul had a hard-on.
Paul raised his hand to his mouth, and licked the sauce on his finger. "Another masterpiece of the culinary arts from my wife," Paul said, and Drew felt Paul start to slightly grind his hips against Drew's ass. Drew moaned, craning his neck to the side and hoping that someone would kiss his neck.
Instead, Paul pulled away, grabbed the two plates and headed into the dining room. "Okay, let's eat!"
Drew was shocked. What just happened? How could he interpret it? What did it mean, both that he had this feelings, and perhaps Paul did too.
Dinner was past mostly in silence, Paul seemingly just happy to eat and Drew sitting in stunned silence. After dinner, Drew did the dishes and Paul watched TV. After drying and putting away the dishes, Drew came into the living room, and sat in a chair, looking at Paul. Paul only occasionally glanced over at Drew, mostly intent on watching TV. After a few hours of TV, Paul got up to go to bed.
"Goodnight, my wife. And remember, tomorrow you must clean my room. And get some thicker hose if you aren't going to shave those legs." With that Paul disappeared into his room.
Drew retired to his room unsure of what to do next. He sat on his bed, in part confused by the events of the day, but also trying to figure out what the next step was. Drew was realizing that he wanted to be Paul's wife, not just for cooking and cleaning, but for some physical affection as well.
Drew looked up, and saw himself in the mirror. In the darkness of his room at night, he could pass for a woman. He had a slender body and nice legs, and with the water bra on, a nice set of breasts as well. He let his hand run down his dress and between his legs, and pulled out his cock. He stroked himself hard and fast, and came quickly. He stood up and turned on the lights, looking at himself in the full length mirror. Drew was right, he did need to shave his legs.
The next morning was smoother than the first. Drew didn't have time to shave his legs in the morning, but he did do a better job with his make up, and had breakfast ready on the table for Paul with time to spare.
As Paul left for the day, Drew walked with him to the door. Paul leaned over and kissed Drew on the cheek, "have a nice day, my wife."
As soon as Paul left, Drew leapt into action. He changed into his street clothes, and went out shopping for the dinner tonight. On the way back to the apartment, he passed a cosmetics store, where a woman was getting make-up applied. Drew walked in and found one of the women who worked there. "Umm, I was wondering if you could help me. I would like to apply makeup to my girlfriend, you know, as a birthday present. Could you help me figure out how to do it?"
The woman looked bemused, but agreed, and started to talk Drew through the procedure. Drew was getting confused though, he really needed to see it happening. "Maybe you could, you know, apply the makeup on me, so I can learn by example." The woman looked shocked, but when she saw Drew was serious, she agreed.
Drew looked good with the professional make-up done, but he had a full day ahead of him and couldn't be walking around outside with make-up on, so he took it all off before leaving the store. He felt confident, though, that he could repeat the process at home that evening.
Drew got back to the apartment and started his cleaning routine. He made sure that he cleaned all the places Paul mentioned yesterday, and ventured into Paul's room. He was making the bed when he noticed the corner of magazine sticking out from under Paul's mattress. Drew pulled the magazine out from under the bed and was shocked when it turned out to be a porno magazine of shemales. So Paul was into this, and by leaving this magazine where obviously Drew would find it was telling Drew that Paul wanted him too. Drew was surprised to find himself happy. He realized that he could get the physical attention he wanted from Paul.
Shadows of doubt crept into Drew's mind by the time he'd finished cleaning though. Perhaps Paul didn't leave the magazine on purpose. Maybe Paul didn't like the idea of getting physical with Drew. Maybe Paul liked guys dressed as girls, but not Drew.
"Damnit," Drew said to himself. "Put that out of your head. There's only one thing to do. Make yourself as feminine and sexy as you can, and seduce that boy!" So Drew went to work. He got in the bathtub, and shaved his legs. He reached the top of his legs and looked at the hair around his cock. What the hell, he thought, and shaved that off to. He didn't have much hair on his chest, but he shaved that as well. He got out of the bath, shaved his face as close as he could, and applied lotion all over his skin. He then dusted himself with baby powder, and went around to applying his makeup. With the lesson that he'd learned at the cosmetics store today, his makeup looked pretty good. He got into his dress and put on his wig, and realized that he looked damn feminine. With his smooth legs, he didn't bother putting on any pantyhose.
Drew got dinner on the go, and waited for Paul to get home. When Paul opened the door, Drew was standing there with a glass of scotch on the rocks. "Here you are, my husband," Drew said, presenting his cheek to be kissed. Paul took the drink and kissed Drew on the cheek.
"Your voice sounds different," Paul said. Drew had made a conscience effort to speak higher and softer to sound more like a woman.
"Oh, really, my husband. Do you like it?"
Paul nodded. "Yes, very soft. Very sexy." Paul sat on the couch, and before his feet were up on the coffee table, Drew was bent down to put on his slippers. This time, Drew let his fingers sensually trace the sides of Paul's feet. Paul let out a slight whimper.
Paul watched Drew gently massage his feet. "Are you wearing nail polish," Paul asked.
"Yes, fire engine red. Very sexy, don't you think. I hope you don't think it too forward for a 1950s housewife." Drew answered.
"No, no, not at all. Very nice," Paul said. Paul shifted in his seat, and Drew noticed the growing bulge in his pants.
"Well, I should get to the kitchen," Drew said, standing up. Drew walked towards the kitchen, making an effort to swing his hips to give him a more feminine walk.
"My wife," Paul called out, and Drew turned around. "I'm not sure I like that dress on you." Drew felt deflated for a second. He thought he had Paul wrapped around his finger, but perhaps not.
Paul wiped sweat from his brow. "I was wondering if you wouldn't mind slipping out of it, and just wearing the apron around the house?" His voice was breaking as he asked it.
Drew smiled, and shimmed out of the dress, revealing his black bra and black panties. He went to the kitchen, and put the apron on. Drew returned to living room, and asked Paul if he liked it.
"Turn around for me?" Paul asked. Drew obliged. "Perhaps just the bra and apron. No panties?" Paul asked, his voice breaking again. Drew slipped the panties down off his hip, and let Paul see his smooth white ass. Paul let out a moan.